How I’m Making Game-Changing Big Life Decisions

Can looking back on your past and applying a snakes and ladders strategy help you make better big life decisions?


I’ve been thinking a lot about some big life decisions ahead of me:

  • Can we keep living between Vancouver and Cape Town, or where do we settle down?
  • Do we have another kid?
  • Should I change the name of this blog? Or should I give up blogging entirely?

Also, and probably more importantly:

  • What game-changing life decisions am I not even considering?

I suppose the question underlying each of these questions is this:

How do you increase your chances of identifying and making the best possible life decisions?

Three Thoughts

If anyone had a surefire answer to this question, they’d be famous, we’d all know it, and the world would be a different place.

Instead, there are a million books and blog posts on decision-making, a bajillion life coaches, and about eight billion people making suboptimal life decisions every day.

Thinking about this while looking for chanterelles on an “empty pocket walk” in the woods with Zac, three ideas came to me:

1. Life is like a game of snakes and ladders.

  • Most life decisions plod you along nowhere fast.
  • Like landing on ladders, some great moves jump you up.
  • Like snakes, terrible choices send you backsliding.

At least this is true for me. A handful of big life decisions largely explain where I’m at today.

2. Aim for game-changing moves.

A smart strategy for life’s game of snakes and ladders would seem to be to:

  • Waste minimal energy fretting over little moves.
  • Focus on hitting ladders and avoiding snakes.

3. Deconstruct and dissect.

Maybe if you analyze the snakes and ladders from your past, you can find common themes.

And maybe you can use those to help you find and make more positively game-changing moves.

Seems sensible, don’t you think?

Let’s see!

I’m going to roll the dice with this exercise and see if it helps me find and make ladder-esque big life decisions.

The Game-Changing Decisions of My Past

(…as far as I can tell.)

Feel free to skim past this extended self-indulgence to see my takeaways and decide whether this exercise is worth trying yourself.

I could have lived here in high school instead of my parents’ basement. (Photo credit: Deensel.)

Turning Down My Grandmother’s Scholarship Offer in 2002

The Decision:

My grandmother offered to pay for me to do my final year of high school at a private school for Canadians in her homeland, Switzerland. I said, “No, thanks,” because I was obsessed with basketball and didn’t want to miss my senior season.

Why It Turned Out to Be a Bad Decision:

What I didn’t realize at the time is that Switzerland has an excellent club basketball system that I could’ve have taken part in.

More importantly, the remaining 98 percent of my non-basketball time would have been more memorable living in Neuchâtel instead of my parents’ basement.

Key Ingredients:

  • Staying put.
  • Saying no without enough consideration.
  • Poor prioritization.

Going All-In to Land a Job With P&G in 2008

The Decision:

Months into a frustrating post-college job search, I decided to give up on landing a job somewhere warm in the US (as an unqualified Canadian, getting a work visa was a no-go) and see if my Swiss passport could help me find something in Europe.

I scored an interview with Procter and Gamble in Switzerland, bought a one-way ticket out there, and brought with me printed-out LinkedIn profiles of every senior manager in the company so I’d know as much about my interviewers as they did about me.

They were impressed. I was hired.

Why It Turned Out to Be a Great Decision:

Working for P&G in Switzerland:

  • Taught me a ton about how to be a professional and how un-special I am.
  • Earned me way more money than I’d have earned in North America, which helped me pile up pretirement savings.
  • Allowed me to travel like crazy all over Europe on the weekends.
  • Enabled me to make friends and connections with people from all over the world.
  • Gave me the opportunity to eat tons of cheese and chocolate.

Key Ingredients:

  • Broadening my horizons.
  • Outside-the-box behavior.
  • Risk-taking.
  • Going the extra mile.
Me drinking a smoothie in Panama.
After-work drinks.

Pushing For a Transfer to Panama in 2011

The Decision:

Even though my boss and his boss told me company policy was against international transfers for employees as junior as me, I didn’t relent. I proved I was worth placating and found an opportunity in Panama City, Panama.

The company was relocating its Latin American headquarters there and looking for staff. I’d never been to Panama before but jumped on the chance to move like a puma on a sloth.

Why It Turned Out to Be a Great Decision:

My years in Panama were some of the best of my life. I accelerated my pretirement savings by earning an expat salary in a lower-cost country, learned Spanish, embedded myself in the Latin American culture, and got to wear flip-flops year-round.

Key Ingredients:

  • Going hard after what I want.
  • Outside-the-box thinking.
  • Risk-taking.
  • Broadening my horizons.

Not Investing My Savings While Working from 2008 to 2013

The Decision:

Even though I’d worked for an investment manager and passed my CFA Level 1, I stashed all my hard-earned cash into a savings account to “worry about later.” I thought my savings were growing fast enough from my salary, anyway. And I had too many other things to do.

Why It Turned Out to Be a Bad Decision:

If I had put my money to work for me while working in corporate, my nest egg would be twice the size today.

Key Ingredients:

  • Short-sightedness.
  • Poor prioritization.
Building this crappy website was one of my best life decisions.
Believe it or not, this took me a looooong time to make.

Building in 2013

The Decision:

One of the first things I decided to do in the “upgrade” stage of my pretirement was teach myself website-building basics by creating an online resume from scratch.

Why It Turned Out to Be a Great Decision:

Getting familiar with the backend of websites made it easy for me to experiment with blogging the next year at Later, after making the regretful decision to give up blogging for a couple years, this led me to this blog.

Key Ingredients:

  • Skill development.
  • Trying something new.
  • Creativity.

Not Buying a Condo in Vancouver in 2014

The Decision:

Following my worldwide pretirement tour in 2013, I returned to Vancouver, where I grew up, to figure out my next move. I seriously considered buying a home there, but decided against it.

Why It Turned Out to Be a Great Decision:

  • If I had bought a place, I would have been a lot more tied down and less likely to move abroad again.
  • I didn’t have enough cash to buy the place outright, so I would have felt the pressure to find a job or make money ASAP to cover my mortgage.
  • Even though Vancouver’s property market went bonkers, I did better with the other investments I made.

Key Ingredients:

  • Favoring flexibility.
  • Trusting my gut.
Chris in Jordan with Kim, maybe his biggest anti-regret.

Joining Kim in Jordan in 2014

The Decision:

The day after meeting Kim on December 27, 2013, I bought a plane ticket to join her and her friend on a trip to Jordan they were planning for the end of February.

Why It Turned Out to Be a Great Decision:

Kim wouldn’t be my wife now had I not done so.

She was visiting from Dubai and I was in living 11,811 km away in Vancouver, so my spur-of-the-moment decision gave us two months to get to know each other long-distance via text, phone, and Skype, then put our relationship to the test with a one-week road trip.

As a bonus, Jordan turned out to be an amazing country to visit.

Key Ingredients:

  • Impulsiveness.
  • Trusting my instincts.
  • Risk-taking.
  • Prioritizing relationships.
  • Going hard after what I want.

Giving “Lifelogging” a Try in 2015

The Decision:

After listening to director Robert Rodriguez talk about the rewards of writing down everything he does on the Tim Ferriss Podcast, I decided to give it a try.

I haven’t stopped since.

Why It Turned Out to Be a Great Decision:

I wrote a post and made a video about the reasons I’ll never stop lifelogging.

YouTube video
How to Make Your Life More Memorable

Key Ingredients:

  • Experimenting.
  • Changing habits.
  • Long-term thinking.

Starting Daily Gratefuls With Kim in 2015

The Decision:

Out of desperation at Kim’s increasingly frequent and emotional outbursts of sadness, anger, and resentment at me, I decided to make a tweak to the gratitude journal concept that was all the rage at the time: I committed to telling Kim one new thing every day about her that I was grateful about.

Why It Turned Out to Be a Great Decision:

I’m pretty sure resentment would have killed our relationship if I hadn’t intervened. Daily gratitude was like penicillin for the infection.

Kim started returning the favor, and we’ve kept it up to this day.

Key Ingredients:

  • Trying something new.
  • Changing habits.
  • Making relationships a priority.

Giving Up Breakfast in 2016

The Decision:

Fed up with the amount of time it took to make and eat breakfast every morning, I stopped feeding myself until the afternoon.

This was before I’d heard all the hoopla about intermittent fasting. It just did it because it felt like it.

Why It Turned Out to Be a Great Decision:

It was my first step toward breaking an addiction to food I didn’t realize I had. I used to snack all the time, everywhere, thinking it gave me energy. Now, I can fast for days and feel fantastic.

I believe fewer meals a day is beneficial for my long-term health, it’s certainly been a boon to my productivity, and the posts I later wrote fasting became some of the most popular on this blog.

Key Ingredients:

  • Trying something new.
  • Changing habits.
  • Impulsiveness.
Walking across a bridge in El Poblado
Kim walking to a café in Medellin.

Moving to Medellin in 2017

The Decision:

Our apartment building in Vancouver was getting torn down, so Kim and I had to find a new place to live. Rather than look for a new home in Vancouver, we expanded our horizons and took the opportunity to go somewhere cheaper, warmer, and more exotic: Medellin, Colombia.

Why It Turned Out to Be a Great Decision:

Not only was Medellin a wonderful place to live for six months, but it was our first step into the world of digital nomadism and encouraged me to commit to this blog full-time.

Key Ingredients:

  • Expanding our horizons.
  • Trying something new.
Me not at all prepared for being a first-time father.
No turning back.

Creating Zac in 2020

The Decision:

Kim and I decided to try having kids in August 2020.

On April 28, 2021, Zac was born.

Why It Turned Out to Be a Great Decision:


Even Charles Manson’s dad probably doesn’t regret having him.

But here’s the thing: If Kim and I had decided to wait to have kids, I know that this alternate universe version of me would be stressed out right now to be 37 years old and childless. Being a dad is a great pain in the ass, and we’re still not ready for it, but it’s better than the alternative.

Key Ingredients:

  • Family first.
  • Leaning-forward.

Three Takeaways

Three common ingredients jump out to me from this exercise of reviewing and dissecting the best and worst decisions of my life.

1. Prioritize Expansion

When I let relatively trivial interests, like basketball or busyness, outweigh bigger ones, I slip up with my decision-making.

So what’s my life’s biggest priority?

I suppose that’s a major life decision in its own right. Maybe the biggest one if I use it to guide all others.

I’ve thought a lot about how I measure success in life and believe for now that my “y-axis” is growth. It seems to be a consistent theme in the past, so I might as well keep using it in the future.

2. Take Big, Impulsive Risks

When I’m between staying the course and changing things up, leaning toward the latter seems more likely to move me up a ladder.

On my pending decisions, that means changing this blog’s name, getting Zac a sibling, and exploring other places to potentially settle.

And, for honing my radar for ladders I’m at risk of cruising right by, I’ve realized it will help to hire someone to help me. For instance, I could use expert support in finding ways to stop plodding and start climbing with my blog. 

3. Try Many Little Experiments for Big Rewards

When little new habits and routines—like lifelogging and daily gratitute—pan out, the rewards can be enormous. And when they don’t, it costs me next to nothing. 

So I want to keep experimenting with new ones. 

With that in mind, I will keep challenging myself to a new 30-day challenge most months. 

Time to Roll the Dice?

Do my takeaways seem obvious?

They are!

But here’s the thing:

Going through this exercise helped me feel these lessons intuitively rather than only know them logically. And “feeling is for doing.”

So I’m going to roll the dice on doing risky stuff that prioritizes growth above all else and may improve my habits.

Will this lead me to make better big life decisions?

We’ll see. For now, at least, I feel more confident it’ll help me find more ladders and fall down fewer chutes.

What do you think?

(Cover image snakes and ladders board image credit: Jacqui Brown.)

About the author

👋 I'm Chris. Everything you read on is my fault. This site is like a gym for your comfort zone, full of challenges to make your status quo sexier. Join my 'Consider This' newsletter for a fun new challenge every 10 days. Try it!

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